Trip in August best timing

Hi,

most likely my new car will be delivered on 1st of August. So I want to take a trip and it fits well as I still have 5 special leave days to kill before September (I do not get national holidays).
Unfortunately August isn't the best month to travel but it can't be helped.

I live in western Chiba almost bordering Tokyo.
Max distance I'd go would be 8hrs in one trip. That would mean up to all Tohoku and probably down to Kansai. Although I'd stagger it. Just in case I have to return suddenly.
But I'm not yet clear on where to go. I only thought the north is probably more cool (temperature) than the south.

So I wonder when is best to go. Right away after 1st of August or maybe some other timing.
I thought it might be good to avoid the time around the national holiday for less crowding and cheaper itineraries.
But I think the closer to September the more dangerous typhoons usually get.
On the other hand there are more in August, which would mean less time for activities outside.

So any input on how to decide where and when to go would highly be appreciated.

Were it any other year, I'd say go toward Niigata and swing up one coast and down the other around Tohoku to catch the amazing Tohoku Sandai Matsuri, but... this year I think they're all cancelled.

Anyway, as you said, typhoon season in late August can make things hard, and the beginning of August really isn't all that much hotter than the end in many places, so if you have to ask for leave in advance like it sounds like you do, I'd say beginning of August. If you choose late then have to cancel for a typhoon, you might lose your days to rain and risk not getting to really go anywhere! Although onsen in the rain can be really awesome, but maybe not typhoon rains...

As for where to go, it really depends; there are a ton of wonderful and amazing places to see, but as most activities, festivals, etc. are cancelled, I'd honestly focus on nature and places like shrines or temples that don't really close. I'd maybe not even really have an objective, just drive surface roads, coastal roads, and see what you find. Doing that, with just an eventual destination and no other plan, have been some of my absolute favorite road trips! But wherever you decide to go, I'm sure it'll be a great trip!

Actually, August is the best time to head anywhere north, just to get away from the heat. Places like northern Tochigi or northern Ibraki are already cool enough, especially at higher altitudes. You can take day trips from there.

Aim for peace in mountains, meadows and onsen. Events are crowded anyway. Do avoid the typhoon, watch out for the weather forecast, and book low-key resorts a week ahead of your departure.

If I were you, the only dates I'd avoid is obon. Expressways and main resort roads would be jammed. Depart just before dawn on a weekday, and you can drive safely and slowly enough while taking breaks until you arrive to your destination by lunch time.

Once you arrive, ask at your accommodation for roads that are less crowded. If you take a PCR test and have a "negative" certificate issued, it might put the people up north at ease.

Thank you for the great input!
You made two very good points I didn't think about yet.
1. if something happens towards the end of the month and I can't take the leave I'll lose it completely
2. taking a PCR test might actually be a good idea (in case things get more though again suddenly)

About the direction...I tend North too. If I'm lucky the weather plays along and I can go hiking a lot. Otherwise I'm sure there's plenty left.

Again, thanks so much!